coprine (CHEBI:3875)

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ChEBI Name	coprine

ChEBI ID	CHEBI:3875

Definition	A non-proteinogenic L-α-amino acid that is L-glutamine in which one of the hydrogens attached to the amide nitrogen is replaced by a 1-hydroxycyclopropyl group. Found in the ink-cap mushroom, Coprinus atramentarius, it causes an unpleasant hypersensitivity to alcohol (the 'disulfiram effect').

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C8H14N2O4

Net Charge

Average Mass

202.20780

Monoisotopic Mass

202.09536

InChI

InChI=1S/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1

InChIKey

OEEZRBUCLFMTLD-YFKPBYRVSA-N

SMILES

N[C@@H](CCC(=O)NC1(O)CC1)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. mycotoxin Poisonous substance produced by fungi. EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor An EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of aldehyde dehydrogenase (NAD+), EC 1.2.1.3.

ChEBI Ontology
Outgoing	coprine (CHEBI:3875) has role EC 1.2.1.3 [aldehyde dehydrogenase (NAD⁺)] inhibitor (CHEBI:35487) coprine (CHEBI:3875) has role metabolite (CHEBI:25212) coprine (CHEBI:3875) has role mycotoxin (CHEBI:25442) coprine (CHEBI:3875) is a L-glutamine derivative (CHEBI:24317) coprine (CHEBI:3875) is a cyclopropanes (CHEBI:51454) coprine (CHEBI:3875) is a dicarboxylic acid monoamide (CHEBI:35735) coprine (CHEBI:3875) is a non-proteinogenic L-α-amino acid (CHEBI:83822)

IUPAC Name

N-(1-hydroxycyclopropyl)-L-glutamine

Synonyms	Sources
(2S)-2,5-diamino-5-oxopentanoic acid	IUPAC
L-coprine	HMDB
N⁵-(1-hydroxycyclopropyl)-L-glutamine	ChemIDplus

Last Modified

08 January 2015